


Lollipop

by mattzerella_sticks



Series: Season 14 Inspired [5]
Category: Supernatural
Genre: Alternate Universe - High School, Awkward Dean, Batman Freeform - Freeform, Cute, DC comics - Freeform, Dean Winchester Has Self-Esteem Issues, Dean in Glasses, Flash freeform, Flirting, Gay Dean Winchester, Halloween, Homophobic Language, Inspired by 14x04 Mint Condition, Jock Castiel, Lollipops and Candy, M/M, Mary cares a lot about her boys, Nerd Dean Winchester, Nerd Dean/Jock Castiel, Toddler Jack, dean gets bullied
Language: English
Status: Completed
Published: 2018-11-02
Updated: 2018-11-02
Packaged: 2019-08-14 15:16:35
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,840
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16495139
Author URL: https://archiveofourown.org/users/mattzerella_sticks/pseuds/mattzerella_sticks
Summary: Dean Winchester isn't the most popular boy in his school. In fact, you couldn't get lower on the totem pole than him. But he's come to accept it, even if it means dealing with people like Gordon every time he tiptoes out of the status quo. Making first impressions is hard given that he's known most of his classmates since the beginning. But besides Charlie, he doesn't have anyone in his corner.Except for Castiel, the school's quarterback who transferred to their school last year. But he'd never go for someone like Dean...(This fic is based around the totally adorable Dean characterization in 14x04)





	Lollipop

**Author's Note:**

> So 14x04 was a great episode, and most of that is because of how cute Dean Winchester was. Seriously, it was the best seeing Dean act so nerdy and happy - I loved it!
> 
> And because of this characterization, I decided to do a little fic with my two favorite tropes - Nerd Dean Winchester and Jock Castiel!
> 
> Enjoy!

            Halloween was Dean’s favorite day of the year, no matter what Sammy thought. Dressing up in fun costumes, watching scary movies – not to mention all the candy! It might have been a few years since he stopped trick-or-treating, but the magic of the holiday still captures him. And even though Dean is in school, he still managed to add a little flair to his outfit. Right now he pulls at his already-loose tie, trying (and failing) to show the rainbow-colored S-symbol on his shirt that’s peeking out from behind his unbuttoned button-down. Luckily he’s not too absorbed in his wardrobe, able to spot the blur of red before it pounces on his back.

            “Happy Halloween!” Charlie shrieks, arms tugging tight on his neck. He chokes out a “Charlie” while he pries her off of him. She doesn’t budge at first, but lets go after a few more seconds of his choking. Dean whirls to face her, red as a bloody corpse.

            “Were you trying to kill me?”

            “Pfft what? Why?” she giggles, “If you died I’d have no friends!”

            He pouts, but accepts her answer. “So, if murder wasn’t your main goal, then why the strangling?”

            “It’s Halloween!” Charlie shouts, oblivious to the stares of the other children, “I thought you might like a good scare to get the day started.”

            Dean rolls his eyes. “I already got that when Sammy forgot to lock the bathroom door.” It was the one time he regretted remembering his glasses on the way to the shower. Seeing Sam reminded him of that one scene from Sleepaway Camp, and Dean wasn’t sure whether to laugh or cry. “Anyway, where’s your costume?”

            “I’m wearing it,” she says, pulling the pointy-eared mask down and tugging her red-and-black cape out to match her wingspan. “I’m committing more than you, _Clark_.”

            “Shut up,” he mumbles, pushing her lightly, “Ma said I couldn’t wear my Batman costume to school. Said something ‘bout it bein’ too _distracting_.” She didn’t say that. When Dean told her his plans for his last Halloween as a high schooler, Mary sighed and forbade him from wearing it. Dean argued with her, but she laid the law in their house. “I just don’t want people to say anything about you,” she told him after Dean stormed into his room, pillow held tight against his chest. “Your costume is so nice, but it’d be too… _much_ for a classroom. And you wouldn’t want something bad said about it after you put so much money into it, now would you?”

            She had a point, but he still wanted to dress up as _something._ His day-costume earned him a sigh and a long hug when she saw it, but that’s all Mary said on the matter.

            “ _Mary_ ,” Charlie groans, falling against the row of lockers next to Dean’s, “Why must you break up the Bat-Duo?!?”

            Dean smiles at her. “Hey, ease up alright? I’m still DC – and I even managed to add a touch of gay.” He pulls at his shirt in a classic Superman pose, cocking his hip the extra inch to Charlie’s delight. Dean lets her laugh wash over him, happy to bring joy to his friend.

            It’s short-lived.

            He’s shoved into the lockers, knocking his head against the metal. His glasses fly off his face from the force, and he bites down the pain.

            “Well, looks like I found Super _fag’s_ kryptonite – _locker_!” The grating laughter clued him in on who caused stars to dance around his vision.

            “ _Gordon_ ,” Dean hisses, squinting at the blurry shapes in front of him, “What do you want?”

            “Just stopping by to say how much we _love_ your costume,” Alistair tells him, the voice coming from his left, “Really captures the whole lonely, gay nerd vibe you send out.”

            “Although if you’re gonna be trick-or-treating, you’ll need something better,” Brady jeers, “No one’ll let you touch their _Twizzlers_ looking like that?”

            Charlie huffs from next to him. “Why don’t you jerks leave us alone, all right?”

            Gordon mocks her with a pity laugh. “No one asked you Bat _bitch_ , so why don’t you step off, huh?”

            “Leave her out of it,” Dean says, drawing the focus back to him, “Just because you can’t deal with your _massive_ crush on me doesn’t mean you get to take it out on her.” He knows he hit a nerve by how the air shifts, the energy tensing and pricking his skin. Gordon grabs his collar and slams his head back against the locker once more, then leans in close.

            “What’d you say to me, Winchester?”

            Dean doesn’t back down. “You heard me. Get any closer and you’ll regret it.”

            “Oh, right – because I’m so scared of the gay kid with the dead dad.” Dean flinches – because of Gordon’s words and the fist that smashes next to his head. Charlie gasps, and he notices more than sees how silent the hallway has become. A fuzzy wall surrounds them, an indecipherable sea of colors and features – as if the blow to the head sent him into a Picasso painting.

            “Now,” Gordon continues, his hushed voice cutting across the silence, “You wanna apologize while you still can?”

            Dean knows he’s not walking away from this without a bruise, and only hopes it’s not bad enough that Mary has to call off work, again, to pick him up. That being said, he chooses to not make it easy for himself. “I’m sorry,” he wheezes, smirking, “Sorry I won’t let you suck my _dick_.”

            “That’s it,” Gordon rears back another fist, “I hope you like _jawbreakers_.”

            He braces for impact – only it never comes. Dean opens an eye, letting the air _whoosh_ out of him when he sees Gordon’s fist inches from his face. Something stopped him before his punch could land, and even with his poor eyesight he can tell his savior has dark hair and broad shoulders.

            It’s when he hears a familiar rumble that he realizes who saved him.

            “Walker,” Castiel says with his cool, ‘I-gargle-rocks-for-breakfast’ voice, “what do you think you’re doing?”

            “Back off Novak,” Gordan snaps at the other kid, “Just teaching this nerd here his place.”

            “You seem to be doing a shitty job, then,” Castiel tells him, “Because his _place_ is as far from you and your neanderthal friends as possible.” The chorus of ‘ _oohs’_ and ‘ _burns_ ’ is nice.

            ‘ _But where were they **before** Cas stepped in?_ ’

            Gordon doesn’t let go. “What’s it to you if we rough up Winchester here?”

            Castiel takes a step back. “Go ahead, then. Do it. But you wouldn’t like the consequences.”

            “You think you scare me?” Gordon chuckles. He puts up a brave front, but even Dean can hear the warble in his response. “What’s a tight ass like you gonna do?”

            “It’s funny,” Castiel says, “how easy it is people write off the things they see on Halloween. They might see a bunch of bruises and blood and think it’s a _costume_. Would you like to test this phenomena?”

            Gordon doesn’t waste any time dropping Dean. He steps back into his cluster; enough that his features start to soften into indecipherableness. But he can sense the hatred in his words. “You’re lucky Winchester,” he spits, “But not that lucky.” He and his friends break through the crowd, dispersing them and forcing them on their way.

            “Dean,” Charlie comes to his side, rubbing his back, “Are you okay?”

            He musters up a false smile. “Yeah… nothing I’m not used to.”

            “Excuse me, these are yours… right?”

            Dean turns to see Castiel standing a little _too_ close. He’s holding his forgotten glasses in his tan blobs. Getting tired of looking through wax paper, Dean takes his glasses back with a small ‘thanks’. Although not seeing Castiel in crisp definition might have made the following conversation easier.

            The blur takes clear form now. Castiel’s once soft jaw hardens, and Dean can make out the small cracks on his dry lips. Notice how the blue in his eyes seems to match the color of his varsity jacket. And his hair, as always, looks as neat and tidy as the storylines on Dr. Sexy. Dean swallows around his heart, and hopes he isn’t blushing too bad. The other boy has been an object of his desires for some time, now, ever since Charlie convinced him to attend one of their school’s football games last year. He didn’t get a good look at him on the field, but after the game was another story.

            Dean was waiting for Charlie, shivering in his dad’s old leather jacket. “Damn Charlie and her tiny bladder,” he muttered, rubbing his hands together, “Why she couldn’t hold it ‘til we got to the pizzeria…”

            “You look cold.”

            He rolled his eyes, and had a smart retort on his tongue. It died there when he got a good look at who said it. “Huh? Oh… yeah. I’m just… waiting for my friend.”

            “Have you been waiting long?” Castiel asked, bundled in a puffy jacket and fuzz-ball hat. Dean realized he had only played football when he did a full-body scan and noticed the grass on his knees.

            “I’m not sure,” Dean said, “But… shouldn’t you be with your team?”

            “Pardon?”

            “I just always thought,” Dean babbled, teeth chattering, “After games a team always stayed together or… something.”

            Castiel cracked a smile at that. “Then I must not have gotten the memo,” he said, “But maybe that’s because I’m still getting used to how things are done here at Carver Edlund?”

            “Oh, you’re new?”

            “Transferred in this year,” he nodded, holding a hand out, “Castiel Novak.”

            “Dean Winchester.” Dean shook his hand, and felt the other boy leave something in it. “Oh, look buddy – I’m the wrong guy to give drugs, too.”

            “What?” Castiel gaped, eyes wide, “No, no – you misunderstood – it’s a Hot Hands.” Dean opens his hand to look at the orange packet Castiel dropped into it. “My mom always seems to give me more than I’ll need and… you looked like you could use it.”

            “Oh, um… thanks.”

            “It was nice meeting you, Dean,” Castiel said, stepping away, “I’ll see you around.”

            “…Yeah.”

            They’ve shared a few more conversations after that, but tend to stick to their social circles. Not from lack of trying. Dean thought about going up to Castiel one day in the cafeteria, but he had took to long and was scared off after Bart called him on ‘staring’.

            “I’m sorry you had to go through that,” Castiel says, shocking him back to the present, “Gordon shouldn’t be allowed to walk the halls without a muzzle.”

            “It’s fine, Cas, really,” Dean tells him, “Gordon’s like a big teddy bear… with teeth and claws and anger management issues.” Neither Castiel nor Charlie laughed at his joke. “I could have handled it?”

            “Before or after he broke your nose, Dean?” Charlie scoffs. Dean casts a wry glance in her direction.

            Dean curls in on himself, pocketing his hands, “Nothing I wouldn’t have dealt with before…”

            He feels Castiel’s fingers tilting his chin up, putting the other boy in his line of sight. “Even so,” he whispers, “Doesn’t mean you should be okay with how they treat you.” Dean’s throat goes dry at that; unable to come up with anything that won’t make the situation even more embarrassing.

            The silence drags on, and soon enough Castiel takes a step back. He scratches at his neck, and now has trouble meeting Dean’s eyes. “By the way,” he continues, mumbling his words, “I – uh… really like your shirt.”

            “What?”

            “Superman?” Castiel points out, “Not my favorite hero but… he’s really cool, too.”

            “Oh.”

            He’s saved by any more awkwardness by the first bell’s ring. Castiel puts even more distance between them. “I should,” he nods his head to the left, “I should get to class. Stay safe, Dean!” Castiel darts away before he could say goodbye.

            Dean barely moves, even when Charlie takes Castiel’s spot. “Well if that didn’t flash me back to Love, Simon…”

            He blinks at her. “What?”

            “Oh don’t ‘what’ me you disaster gay,” Charlie chuckles, “He’s got a thing for you.”

            Dean blushes at the notion. “That – that’s crazy,” he stammers, “How could you – he’s not – it can’t be –“

            “Dean, why do you think he doesn’t?”

            “Because!” He glances around and leans close to her, whispering. “Because… he wouldn’t be interested in _me_.”

            Charlie sighs, and then tosses her arm over his shoulders. “We gotta get your confidence up one day, otherwise we’ll never conquer the seven kingdoms of Moondoor, my dear Handmaiden.”

            “Charlie…”

            “Let’s just get to class.”

            He lets Castiel and his haunting, blue eyes drift towards the back of his mind. 

* * *

 

            “No! But we…we killed you!!!”

            Dean laughs as the girl screams her head off and rushes down the hallway from Hatchet Man – albeit not far in those heels. He sticks his hand into candy bowl and pulls out a bite-size piece of chocolate, unwrapping it and popping it in his mouth. Dean smiles around his as Hatchet Man’s victim trips over nothing in her haste. “God,” he chuckles, “They don’t make ‘em like this anymore.”

            Just as she starts to make her way towards the elevator, the doorbell rings outside. Dean sighs and looks towards the door in annoyance.

            He knows he’ll have to answer it. There’s no one else but him at home. Sam had been invited out with a few friends, and Mary was dropping him off before going to a costume party at the Mills’.

            “Are you sure you don’t have to go anywhere?” Mary asked him before she left, pulling her coat tight around her cowgirl outfit, “No special plans with _friends_?”

            “Charlie said she had to finish a project for her Coding class, so she’s too busy to hang.”

            “And there’s… no one else?”

            “Ma, it’s okay – I mean, someone has to hand out the candy, right?”

            “We can leave the bucket out with a sign if you’d rather be doing something else?” Mary tries one last time, “Maybe if Sam asks his friends…”

            Dean winces. “I don’t wanna crimp my baby bro’s style. Besides, if I show up they might kick him out because he’s the less awesome Winchester.”

            Sam walks into the room at that comment, and levels Dean with a flat look. “Yeah, because _I’m_ the one in the replica superhero suit.” Dean crosses his arms, or as best he could in his Batman costume.

            After the rough day at school, which only felt worse since everybody stared at him and whispered behind his back more than usual, he traded in his button-down for the Kevlar and spandex. It’s a special costume – hand-made for him by a person down in Texas. The cost wasn’t _that_ much – in fact, he managed to pay Mary back after a full summer down at Singer’s Auto Repair Shop. It was worth it, since stepping into Batman’s boots made him feel cooler, more badass, and most importantly – safe.

            Although there’s probably nothing cool about a teenager in a Batman costume lounging on a sofa.

            The doorbell rings again.

            “Alright, alright, I’m coming!” he grouses, pulling himself up. He tosses his glasses off and tugs the cowl over his face before opening the door.

            On the other side of the door is a little boy dressed as Luke Skywalker, gaping up at him, with his bag’s straps loose in his little fingers. Dean fights back a grin, not wanting to ruin the act. The other reason Dean had wanted to stay home was because the suit always got him compliments. Little kids figured he was the real deal, and their guardians always flashed him a smile or nodded as he played along with the children. He’s even recognized a few kids from school give him compliments.

            Dean’s not sure they knew it was him under the mask, however. If they did, they might not have said anything nice.

            “Hello, Luke,” Dean starts in a low growl, “Are you here because you sensed something in the Force?”

            The question snaps the boy back into focus, and he remembers what he came here for. He giggles, and holds out his bag. “No Batman,” he says, smiling with three-fourths a smile, “It’s Halloween!”

            “Halloween? Ah yes… that makes sense,” Dean smirks, looking away, “And you want me to go out and stop criminals! It’s about time I start patrol…”

            “ _Noooo…_ ”

            Dean bends down as much as he can, to meet the kid on his level. “Then what should I do?”

            “Give candy!” the kid pushes his bag out once more, “Trick-or-treat!”

            “Candy? But candy is for good little boys and girls who uphold the law,” Dean offers the boy a stern look, “Do you promise to do just that?”

            “Yes Batman!”

            “Then here is your candy.” Dean grabs a generous amount and drops it into the boy’s almost full bag before standing to his full height. He watches the boy search his bag with a bright smile. The boy shares it with him.

            “Thank you, Mr. Batman!”

            “It’s no problem,” Dean says, “Just a hero doing his duty.” He’s about to return to his movie when a deep chuckle draws him out longer than he intended. Dean sets his sight on the bright, red blur standing a few feet away from Luke. He squints, making out a yellow lightning bolt on his chest. The symbol clues him in that the guy’s supposed to be the Flash, but it’s his next words let him in on who’s behind the mask.

            “You seem to be very good at your job… Batman.”

            ‘ _Holy shit_ ,’ Dean thinks, mouth falling open slightly, ‘ _Is that… Cas?_ ’

            “What can I say,” Dean grimaces, “Batman’s good with kids.”

            “As he should be,” Castiel chuckles, “To have raised four…”

            “Yeah, um…” he clears his throat, “is Luke here your brother?” The younger boy is oblivious to the conversation, chomping his way through a full-size candy bar.

            “What? Oh, no,” Castiel looks over at the boy, “Jack’s my nephew. My brother Luke is laid up with a cold so he couldn’t take him trick-or-treating so… here I am.”

            “Ah.”

            “You know, you’re the first person to guess brother?” Castiel continues, “People kept asking me if he was my son…”

            “Yeah, well… you don’t look old enough to have a kid,” Dean chuckles, “but you _do_ sound like you would.”

            “That might be true,” Castiel says, “My brother says I have the voice of a chain smoker.”

            “Luke?”

            “No, Gabriel.” He pauses. “What about you?”

            “What about me?”

            “No other plans besides manning the door.”

            Dean bristles at that. “It’s not glamorous, but somebody has to do it. I’m sure there’s probably tons of parties _you_ could be at right now, too.”

            He doesn’t see the look on Castiel’s face, but Dean notices the red get closer. “I… I didn’t mean to offend,” Castiel says, “It’s a good thing you were here… the past few houses were just bowls of candies and signs. You, answering the door… it’s brings a human element back to Halloween.” The words send a chill up Dean’s spine no horror movie could ever accomplish.

            “Yeah, well…” Dean fumbles, holding the bowl up high, “thanks. Want some candy?”

            Castiel reaches forward and rustles through the candy before pulling out a lollipop as red as his costume. He takes his time unwrapping it, slowly pushing it past his lips. Dean’s suit, made to fit him perfectly, feels uncomfortable.

            “Cherry,” he says, “My favorite. Thank you, Dean.”

            It takes a few seconds for Castiel’s words to register. He almost drops the bowl. “Cas you – you recognized me?”

            “Of course,” Castiel grins, “There’s not that many boys our age who would invest a lot of money in a suit like ours.”

            “Like _ours_?”

            “Oh – you aren’t wearing contacts?” Castiel asks, “I figured with the suit…”

            “I mean, I don’t wear the mask indoors,” Dean explains, “And I don’t usually get into conversations with the people I’m handing candy, too.”

            “That’s fair…” Dean squirms, unsure what the next step in the conversation is. He’s not good at this, and doesn’t want to say something that would be like walking into quicksand. Castiel takes the decision from him.

            “You know, I like this costume better than your earlier one.”

            “You do?”

            Castiel hums. “Indeed. Batman is one of my favorites.”

            Dean cocks his head to the side. “Then why’re you dressed as the Flash?”

            “I said he was one of my favorites, not my _favorite_.”

            “Oh,” Dean says, rubbing at his neck, “Yeah… Flash is pretty cool, too.”

            “Yes…” Castiel pulls his lollipop out and takes a step closer. “Hey, Dean, have you ever heard of Batflash?”

            “I… I don’t think I have?”

            “It’s the romantic coupling between _Batman_ ,” he gestures to Dean with his lollipop, “and _Flash_ ,” he points back to himself. “Some people like to think that the relationship is strictly platonic but… well, I would say otherwise.”

            “You would…” Castiel’s intention strikes Dean in the back of the head as if it were a baseball bat. “ _Oh_.”

            The other boy leans fully into his space, enough that he can see Castiel’s pink-tinged smirk. Castiel pushes the lollipop into Dean's mouth, and moves towards his ear. “I’ll be bringing Jack back home soon, and after that I don’t have anything else planned.”

            “No… no parties?”

            “None that’d make me want to be anywhere but here.” Dean softly moans around the candy. “So, if you’d like… I could come by and teach you the finer points of the ship?”

            He nods.

            “Very well,” he says, stepping back, “Keep that safe for me. Jack?” The smaller boy looks up with chocolate-stained cheeks, and offers another goodbye to Dean.

            Dean watches them fade into the fog of the night as he tries to process what happened. 

* * *

 

            The house is dark and quiet, the television screen long since muted. Now teens from generations ago silently scream as they face down their doom. Mary opens the door slowly, stepping into the darkness, boots in hand. “Dean? Dean, I’m sorry I’m late but Donna wouldn’t let me leave without showing off her pictures from her trip to Aruba last spring.” She turns on the light. “Dean – oh!”

            Mary can barely contain her grin at the sight on her couch. Dean, still in his Batman costume, has fallen asleep, nestled in the arms of another boy. She thinks he’s dressed as the Flash, but she’s never been as good at the superhero names like John was. The other boy has his nose pressed firmly into the crown of Dean’s hair, and there are candy wrappers scattered between them.

            “Oh thank you all that is great and merciful,” she sighs, tearing up at the sight of her boy’s contented smile.

            The warm feeling fades, replaced with a more mischievous thought. She takes out her phone and snaps a quick picture. “Sam’s going to be so pissed he missed this.”

            Mary forwards it to her youngest son before heading off to bed.

            ‘ _A great Halloween indeed_.’

**Author's Note:**

> You like?
> 
> I'll admit, I was debating on using the Red Hood costume (because Jensen's photos <3) but seeing Dean drink out of the Flash mug I decided to use another of my favorite ships!
> 
> Drop a kudos/comment if you had a good time reading!!


End file.
